Dog Boarding in Countryside Woods, Clearwater, FL
Find a loving dog sitter to watch your dog overnight at your sitter's home.

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Top rated Countryside Woods dog boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“I had a great experience boarding my girl with Laura. From the day we meet to see how my girl would react to the time she took care of her. She kept me updated with pictures from the park,walks and even if she didn't look something right. Loved how she had her place ready for my girl and her family also took care of her like it was her own. My girl is a 80lb pitbull, and yes she was loved every moment she was there.”

“Heather and her family were so great with our little dog. She was super easy to get in touch with, sent updates on how the dog was doing, and made drop off and pick up a breeze.”


“Great experience with Mike. He watched our three pups this last week which included our young puppy. Mike updated us every day with pictures and let us know how they were all settling in. One of my pups had a medical emergency while there (a seizure) and contacted me immediately while en route to the emergency vet. He made sure to keep me updated and calmed my nerves while I was away from my pups. I can highly recommend Mike and I am already re-booking him again for a weekend next month when we go out of town. Thank you again Mike for taking such good care of my pups!!!”

“Athena & Richi Took great care of our beloved snoot while we were in France! He was very tired when we picked him up he must have had a great time with all the other pups there! We would recommend them to anyone needing a dog sitter!”


“Lou was great!! I feel fortunate that I was able to have him care for my fur-baby. Lou knew what to do to make my dog comfortable and eat. Gordie (my dog) is very picky about eating but loves to sit with somebody on the couch and sleep in bed with them. Lou did all that with him to make Gordie feel better away from home.”

“We left our 2 dogs with this wonderful couple for multiple days. Their home is clean and comfortable. Our dogs came home happier than ever! Can't beat the great communication and peace of mind. Will use them again!”

“Jason did a fantastic job with our pup Nugget. He gave us daily updates, and I had peace of mind knowing our pup was in good hands. I would highly recommend Jason, you can tell he is a real pet lover! We will def be bringing nugget back the next time we are away!”

“Jean was extremely pleasant and a fantastic dog sitter (along with her husband Bernie). I couldn't have been luckier to have found her to take care of my aging dog. We were out of the country for 3 weeks and Jean sent me pictures and updates every day. Our dog was very well taken care of and I would not hesitate to use her again.”


“Brett did a great job watching Nimbus for us! He sent many pics and kept me updated with how Nimbus was doing. He was able to give Nimbus his medication. Nimbus was a happy and tired boy when we brought him home. Thanks Brett!”
“Staying at Ashleigh’s home was a great experience. She is very welcoming, friendly, and affectionate with animals. Her place is well-organized, with dedicated areas and plenty of space for play. She sent daily photo updates while Oreo was there, and truly proved to be an excellent caretaker. Ashleigh was so sweet that she even put a bandana and a little bow on Oreo. Oreo seemed very happy during her stay, and we’ll definitely be booking with Ashley again for future stays.”

“I had never used Rover before and my husband and I were going on a 7 day Alaska cruise and checked into boarding facilities and due to Toby not neutered, he couldn’t be with other dogs and Toby is a very loveable, playful dog and loves to be around people as we are home all day ourselves. I saw Lana’s bio on Rover, and I liked what I read, and wanted to meet her with Toby before I committed to her watching Toby for 10 nites. My husband and I with Toby went to meet Lana, and her Husband was there and they were very welcoming and we chatting for a bit, and were very comfortable in Lana watching Toby while we were in Alaska. Lana, sent pictures and gave us updates on Toby, which was very reassuring to us, that Toby was happy and being taking care of in a loving home, until we return from our Alaska Cruise. I would recommend Lana, highly, and in the future when we plan another vacation, we hope she will be available to watch our precious Toby!”

“Norma and her sweet family were wonderful and exceeded any expectations we had. They treated our dog like an absolute princess. We received many pictures and in every photo we could see how happy our dog was. They welcomed her with much love and warmth. I would highly recommend Norma!”

“Jessica and Colin watched our pup, Hazel, recently and did a great job! Hazel had a great time at their home with their adorable family. Jessica was quick to respond every time I texted , and was very flexible. We will definitely be using Jessica and Colin again if they are available. They are trustworthy, responsible and reliable . Hazel can’t wait to go back! 🐾”

“Leslie did a fantastic job work with Coda. She was very attentive of her blind eyes and taking her insulin before meals. I received plenty of updates and pictures over the one night stay as well. Highly recommend and will use Leslie again in the future.”


“This was my first time using Rover and Jennifer was absolutely amazing! She messaged me everyday with updates and pictures/videos of how Chloe was doing. I couldn’t ask for a better experience! Jennifer truly cares for animals and goes above and beyond to make sure your pet is well taken care of! I highly recommend her and will be using her again in the future!”

Countryside Woods dog parents share their Rover experiences
Izzy is amazing. I knew the moment I met her she would be perfect for my Clarkie. He loved staying with her and was excited to play with new friends. We will definitely use Izzy again. Highly responsible and so loving. Thanks, Izzy for making Clarkies stay fun and giving me peace of mind when leaving him. ❤️

We had an excellent experience with Lori while she cared for our dog, Joey. From the very beginning, Lori was professional, communicative, and genuinely caring. It was clear that Joey was treated like part of the family, and we felt completely at ease knowing he was in such good hands. Lori provided regular updates and showed true attention to Joey’s needs, personality, and comfort. When we picked him up, he was happy, relaxed, and clearly very tired from all the playing he did. We highly recommend Lori to anyone looking for dog boarding experience. We will absolutely be using her services again.

I was visiting from out of town and needed a dog sitter, which is incredibly nerve wracking! Tuany put me at ease - she’s a pro with a set approach in meeting and greeting us, sending photos, etc. She cared for Dixie like she was her own which is very much appreciated!

First off I have to say that I am very nervous about leaving my dog with anyone (heck even my own mom). That being said, within 2 minutes of our meet and greet I felt comfortable with Patrick watching Tessa. You could tell how much he loved and cared for all animals and it's something my dog picked up on right away as well. Upon meeting Patrick for the first time Tessa did her usual look around and then proceeded to go straight to Patrick as if she had known him for years. I received multiple updates and pictures everyday and could tell Tessa was very comfortable staying with Patrick. When I finally got back from my trip, Tessa was clearly well taken care of and happy. Patrick is absolutely the first person I will contact in the future if I need someone to watch my dog again!

Penny just got home from Paige and Stephen’s and is already sleeping like a baby which I know means she had a great visit. Our deaf senior girl is always comfy in their home and she’s a picky dog. We always miss her when we are apart but never worry about her when she’s with these guys.

Sarah and Arabella were phenomenal. Sarah has a lot of knowledge on dogs and how to’s. My pup loved being there and I can tell by his demeanor when I pick him up and it was night and day from my last sitter. I highly recommend these two and will be rebooking with them for sure.

Lindsey and Brady were fantastic! They were extremely communicative and kept us updated with plenty of messages and photos. We really appreciated that they invited us into their home at drop-off so we could see where our pup would be staying—it immediately put us at ease. Our boy was clearly very well cared for, and we couldn’t be happier. We’ll definitely be using Lindsey and Brady again moving forward!

I had such a great experience with Angie. She took amazing care of my dog and kept me updated with pictures and messages the whole time. I felt completely at ease knowing my pup was in good hands. Highly recommend and I have already booked her again! She’s the best!

These guys are wonderful! They shared details and pictures all throughout Millie's stay, and I appreciate that they tell you the good and the not-so-good details because it shows they are very trustworthy and truly care about your dog. We will definitely be reaching out again!

Luna had the best time at Denise and her sweet doggie Frankie’s home! She has the perfect fenced in yard for the dogs to play and they are never left outside alone. She also makes sure the gates are locked for safety. Denise sent photos throughout the stay and kept in touch frequently. I can’t wait for Luna to return! Thank you Denise and Frankie

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1. Search
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Why Choose Rover?
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Reservation protection
It doesn’t happen often, but if your dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.
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We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Dog Boarding FAQs
Frequently asked questions about Rover
Typically, dog boarding sitters on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your dog in no time!
Experience can vary widely from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when comparing sitters available in Countryside Woods.
Rover makes it easy to find Countryside Woods dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:
- Dogs of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog boarding sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.














